


Pretty in Pink

by glittergothfae



Category: Critical Role (Web Series)
Genre: Bondage, F/M, Face-Sitting, Femdom, Light Bondage, Lingerie, Plot What Plot/Porn Without Plot, Praise Kink, Rope Bondage
Language: English
Status: Completed
Published: 2019-03-03
Updated: 2019-03-03
Packaged: 2019-11-08 15:35:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,265
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17983835
Author URL: https://archiveofourown.org/users/glittergothfae/pseuds/glittergothfae
Summary: In the spirit of being transparent, it had been much too easy to coax Caleb into his current state; that is, tied to Jester’s bed loosely and wearing one of her more frivolous, lacy pairs of underwear.





	Pretty in Pink

In the spirit of being transparent, it had been much too easy to coax Caleb into his current state; that is, tied to Jester’s bed loosely and wearing one of her more frivolous, lacy pairs of underwear. 

It had started with the bit about the underwear. Jester had meant it as a dare, though she was genuinely curious about how stunning Caleb would look in pink.

“Cayleb?” She’d called despite his being just on the other side of the room.

"Ja?” He didn’t even look up from whatever book he was reading; Jester thought she’d seen something about vocabulary on the spine earlier.

“I dare you to wear a pair of my underweaaar.”

That made him break from whatever linguistic knowledge he’d been trying to soak up. A blush sparked on his cheeks and for a moment Caleb didn’t say anything at all. 

Then, he finally managed to blurt with complete seriousness, “Which pair?”

Jester grinned and raced to find the exact pair she’d had in mind. They were pink, lacy, and (here, Jester’s grin grew even wider and somehow more devilish) just small enough that they would probably cause some amount of overflow.

When she returned, she waved the pair in front of Caleb, bouncing ever so slightly with her excited movements. “This is the pair!”

Caleb studied them briefly. It wasn’t like he had never seen them before (he’d definitely seen them on Jester a few times, maybe more). He wrinkled his nose and Jester worried that she’d made him uncomfortable.

“Aren’t these some of your favorites? Wouldn’t you be worried about my ruining them?” He inquired.

“Cayleb, that is absolutely not the point!” Jester pouted. “I already know what they look like on me. I want to see how beautiful you are in them.”

The wizard in front of her blushed an even more brilliant red than before and quietly said, “Only if you’re sure you don’t mind me wearing them.”

“I wouldn’t have dared you to if I did, would I?”

“No.”

“Then go put them on!”

The terms of Jester’s dare involved Caleb wearing the pair for an entire day. Jester internally relished the thought every time she looked at him throughout their day. He’s wearing my underwear! She thought, barely containing the happy bounce she wanted to outwardly express. He’d modeled briefly for her after putting them on and Jester still thought about how gorgeous he looked in lace (and how much overflow there was).

She wasn’t sure, but she almost swore on occasion that he tried to discreetly fix what she could only imagine was either unfortunate pinching or a wedgie. That latter option made it very hard not to laugh.

Finally, when it was time to retire for the night, Jester had even more planned.

“Now, Cayleb, you’ve been a very good boy wearing my underwear all day. Would you be willing to do something else for me?”

That next favor was how he’d ended up tied to the bed. She’d asked with incredible trickery in her tone; Caleb automatically knew that meant this would result in a rather interesting evening. So, without hesitation, he undressed (save for the panties, per Jester’s orders) and Jester restrained him lightly. He’d said before she could tie the ropes tighter, but she refused; she was genuinely afraid of hurting him—or even worse, that he would let himself be hurt by it and not tell her. They trusted each other implicitly, but Jester knew all too well that Caleb could sometimes punish himself for the past and she would have no part in it. Her sweet, somewhat grubby wizard would be nothing but pampered and praised if she had a say in this.

With that semi-permanent devilish grin still stuck on her face, Jester started grazing her fingers up and down Caleb’s thighs. She couldn’t be sure, but she thought he let out a sharp gasp as soon as she got just close enough to where he was practically popping out of the panties. With this knowledge, she breathed right on top of his balls, hoping that got more of a response. He wriggled slightly beneath her, and Jester decided to up the ante again.

“We’ll count this as an ‘entire day,’” She whispered as she began to slowly remove her underwear.

She made sure to snap the waistband slightly before they left Caleb’s hips. He groaned under his breath and Jester giggled while peppering kisses on his thighs.

“You’re so vocal, Cayleb. I do love hearing how pretty your voice is.”

This, is some part, gave her the next idea. Once the panties were off, Jester moved. She trailed fingers up from his throbbing cock to his nipples (which Jester tweaked just a tad) while she positioned herself. She placed her thighs on either side of Caleb’s head and made her intent to stay there perfectly clear by wrapping her tail around the base of his dick.

“Would you be a good boy and eat me out until I ask you to stop?” Jester phrased it as a question, but Caleb knew it was a polite request.

“Of course, Jess.” His voice was slightly muffled by Jester’s form above his mouth, but his tongue proved this was clearly what he said.

While Caleb’s tongue somehow used the exact pressure Jester wanted, she began working her tail to tease him even more. She could feel the slightest bit of precum dripping onto the tip of her tail and smiled as Caleb moaned while latched onto her clit. She stopped whenever she could feel him making the movements he usually made when he got close to an orgasm and this made Caleb much more vocal than usual.

“Please, Jess. Pleaaaaase.”

“Please what?”

As quickly and loudly as a shout, Caleb replied, “Please, Mistress.”

Immediately, Jester stopped. Her eyes met his and she could see the familiar blush on his face. She’d intended for him to say something like “Please don’t stop” or “Please fuck me.” But this was also good.

“Oh, Cayyyleb, what a wonderful way to ask. Would you keep calling me ‘Mistress’?”

He quietly replied with a mumbled affirmative and she told him to resume that lovely thing he was doing with his tongue. He certainly did; his tongue swept from her folds to Jester’s clit and felt like pure heaven.

This started a routine. Caleb would continue to call her Mistress, but as soon as he slipped up and used her real name (or any form thereof), she stopped working her tail around his cock. Finally, after a couple of leg-shaking, incredibly wonderful orgasms, Jester felt it was time for Caleb to get some relief.

“Would you like to come, Cayleb?” She asked. “You’ve been so good for me that I think you’ve earned it.”

“Yes, please,” He groaned.

“Please…?”

“Pleaaaase, Mistress!”

Jester smiled and cooed, “Oh, Cayleb, you’re a lovely boy. Now come for me.”

Caleb made the biggest sigh of relief when she finally used her tail to tip him over the edge. She climbed off his face, noticed the (rather large) amount of cum spread across his stomach, and helped clean him up. She repeated her previous praises and peppered his face in kisses before they both settled in to get some rest. With familiar grace, Jester assumed position as the big spoon, and she kissed Caleb’s shoulder with the swell of affection she always felt holding him.

“Cayleb?” Jester asked quietly (though much in her tone from the beginning of this whole ordeal). 

“Ja?” He returned quietly.

“You should keep that pair of underwear.”

**Author's Note:**

> Bless the Widojest server.


End file.
